


Valentine's what?

by KissingWinchesters



Category: Supernatural
Genre: Anal Fingering, Anal Sex, Butt Plugs, M/M
Language: English
Status: Completed
Published: 2021-02-13
Updated: 2021-02-13
Packaged: 2021-03-13 22:53:21
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,020
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29409366
Author URL: https://archiveofourown.org/users/KissingWinchesters/pseuds/KissingWinchesters
Summary: Sam and Dean make a bet that neither of them can touch themselves or each other until Valentine's Day. Not so easy when one of them is walking around with a butt plug in their ass.
Relationships: Dean Winchester/Sam Winchester
Comments: 8
Kudos: 86





	Valentine's what?

**Author's Note:**

> First collab for sn_specials with amazing art by my fab friend merakieros. Always fun to do these challanges and I think this one turned out good :) was fun to write!
> 
> Here is the[Link](https://merakieross.livejournal.com/17510.html) to her art! Oooooooh it’s a beauty!

“You can’t touch me, remember?”  
  
Sam’s whole body tenses, sensitive even to the movement of air when Dean comes up behind him.  
  
“M’not. Just looking for something.”  
  
Dean purposefully reaches around Sam’s arm, fingers idly running over the tops of the Manila files in the cabinet Sam was sorting. He’s not even trying to be looking for something. He’s just being a dick.  
  
Sam starts to sweat, the plug in his ass shifting slightly as he tries to put more space between them. It’s not that Sam doesn’t want Dean touching him, he’s fucking desperate for it, but there’s no way in hell he’s losing the bet. But, if Dean so much as “accidentally” brushed against him again right now, Sam wouldn’t be responsible for his actions.  
  
“Hm, nope must be someplace else,” Dean says eventually. He sounds turned on, which makes Sam feel smug at least.  
  
“You won’t break me,” Sam says, turning around once he’s sure Dean has backed off.  
  
Dean laughs, all sharp teeth and lines around his eyes, and Sam feels his cock twitch and wants to kick Dean really hard. And then, Dean has the nerve to sit down on the desk and spread his legs.  
  
“Sam, I swear, I was looking for something. You just happened to be in here.”  
  
“You’re such an ass,” shaking his head.  
  
“What?” Dean laughs. “Look, if you’re struggling with this, just say the word.”  
  
Sam makes the mistake of clenching, and the sensation of it makes him involuntary moan.  
  
Dean stands up and Sam all but runs out of the room.  
  
“Sammy, come on,” Dean says, following close behind. “You’ve had it up there a few good hours now, it’s nothing to be ashamed of if you want me to take it out for you.”  
  
“Shut up, Dean. Go away.... ahh, oh god.” Sam continues to curse as the plug moves, and he has to stop walking to lean against the wall, his pulse beating wildly.  
  
Dean circles around him, leaning on the wall facing Sam. His eyes are a little unfocused, and his bottom lip is getting swollen from biting it so much.  
  
“Feelin’ ok?”  
  
“Are you?” Sam says.  
  
He drops his eyes to Dean’s crotch but there’s no obvious signs of him being hard. It annoys the hell out of him. Here he is, suffering with pent up arousal and all Dean has to do is keep his hands to himself until tomorrow, fucking Valentine’s Day, and he wins the stupid bet that might have been Sam’s idea but he’s so damn horny he can’t actually remember.  
  
In any case, Sam is suffering and Dean is a massive jerk.  
  
And that’s when the lightbulb moment happens.  
  
Since when does Dean ever really win against him? He’s said it himself, many times, that one look at his big puppy dog eyes and Sam could get people to walk through fire for him. Most of all, his big brother.  
  
Trying not to show his smile, Sam covers his mouth with his hand.  
  
“Uh, I’m gonna... I got all dusty in there. I’m gonna go change.”  
  
Pushing off the wall, Sam passes Dean, deliberately going as near to him as he can without touching. Dean follows him of course, but the tables have turned, and now Sam has realised that although he might be the one with the silicone plug up his butt, he’s also the one with all the power.  
  
Walking into his bedroom, Sam sheds his shirt, tossing it onto the chair by the bed. He hears Dean close the door, and because he’s got his back to him, Sam smiles freely. Dean is so fucked.  
  
“Rules are rules. Can’t touch yourself either, little brother.”  
  
Sam snorts a laugh and turns around.  
  
“Kinda gotta touch myself to change my clothes,” he says, teasing at the hem of his T-shirt before slowly pulling is up and over his chest.  
  
His nipples are hard, have been since he put the plug in that morning, and he hisses when his wrist grazes one of them.  
  
“Stop it,” Dean says, clearing his throat. “Unless you can’t help yourself?”  
  
“Just changing my clothes,” Sam reminds him. He throws the t-shirt on top of his shirt then pulls off his boots and socks. “If it’s too much for you, you could just leave, you know. You don’t have to be standing there watching me if you can’t control yourself.”  
  
Dean chuckles like Sam is being ridiculous, but his cheeks and ears are flushed pink, and there’s definitely a bulge starting between his legs.  
  
“I’m just fine. I can wait a few more hours, no problemo.” Dean looks at his watch and frowns. “Ok, more than a few.”  
  
“How many?” Sam asks, his hands still on the button of his jeans. He’d put the plug in at around seven that morning, after they’d come up with the stupid bet while in bed, and time had pretty much lost all meaning after that.  
  
“Uh... ten hours and eight minutes. Fuck.”  
  
The last word is quiet, but Sam hears it loud and clear. Dean is going to snap.  
  
“Ten hours.” Sam undoes the button on his jeans.  
  
“And eight minutes,” Dean says, his eyes on Sam’s hands.  
  
“Easy, right?” Sam pulls down his fly and turns around. His jeans fall a little, revealing just the top curve of his ass. “Uh, maybe you’re better off leaving? I don’t have underwear on and...”  
  
“What? Sam, you wiggling your butt at me isn’t going to make any difference. I don’t lose bets. I don’t lose...”  
  
Sam pushes his jeans down further, holding them on his thighs so they won’t drop to the floor just yet.  
  
“Yeah? Wanna play rock, paper, scissors?” Sam laughs, looking at Dean over his shoulder.  
  
Dean licks his lips, his Adam’s apple bobbing as he swallows. Sam knows Dean’s done for when he doesn’t even snark back.  
  
From that angle, Dean would be able to see the base of the black plug, but Sam bends forward slightly just to be sure, letting his jeans drop finally and stepping out of them.  
  
The coolness of the room combined with Sam’s overheated body makes for a feeling of overstimulation that gets him a little crazy. Sam breathes in deeply, rolls his shoulders, the pressure in his ass a constant throbbing pleasure.  
  
“No, no, no, you can’t lie down. No touching, remember? That means both of us.”  
  
Sam’s legs connect to the edge of the bed, and he folds his body down, palms flat on the mattress. He opens his legs wider, getting his knees up onto the bed.  
  
“I’m not touching. There wasn’t anything in the rules about not being allowed to lie down on my own bed,” Sam says. He keeps his ass in the air, curving his back and using his arms as a makeshift pillow.  
  
“Sure there wasn’t a rule about putting on a show, Sammy?”  
  
Dean’s voice is low, and Sam can feel the intensity of his brothers gaze. He’s hyper focused, watching every move Sam makes, every twitch of muscle, and Sam’s skin prickles with pleasure because of it. There’s nothing like the power of Dean’s attention.  
  
Slowly, Sam looks back towards Dean.

  
  


“Sit down.”  
  
Dean doesn’t move for a moment, but then he takes a few steps to the chair, shoves Sam’s clothes onto the floor, and then pulls it to the foot of the bed. He sits down and spreads his knees.  
  
“How’s it feel?”  
  
Sam breathes in through his nose, clenching around the plug. His cock is leaking, dragging against the sheets.  
  
“Like you... just not as good.” Sam digs his fingers into the bedding. He sees Dean lay his hand on his inner thigh. “It’s not as big as you. Doesn’t fill me like you.”  
  
Sam shifts his knees, pulling his ass up further so that his cock hangs between his legs and away from the sheets. He doesn’t want any contact to make him do something stupid like grind against the bed, even though he’s desperate to.  
  
“Makes me ache everywhere,” Sam continues. “It’s like... when you eat me out, fuck Dean, I can’t take it but I don’t want you to stop.”  
  
Sam watches Dean’s hand lift up to the hem of his shirt, pushing it up over the top of his jeans. He’s hard, Sam can see well enough from where he is.  
  
“Don’t touch,” Sam says, turning his head even more even though his neck is burning.  
  
“Just making room,” Dean replies. He opens his fly, folding the denim down so that Sam can get a better look.  
  
Instead, Sam buries his face in the pillow, rolling his shoulders and tightening the muscles in his arms. His cock is throbbing almost painfully, and Sam bites down on his lip to distract himself. Dean is holding out a lot longer than Sam expected. He’d thought Dean was going to tackle him to the bed as soon as he’d taken his clothes off.  
  
Breathing heavily, Sam lifts his head and pushes his hair out of his eyes. Letting his knees slide down, Sam lies flat on the bed, his ass squeezing the plug even more.  
  
“Dean?”  
  
“Mm?”  
  
“Why did we make this stupid bet?”  
  
“Um... wasn’t it something to do with Valentine’s Day?” Dean frowns, like he’s not entirely sure.  
  
“Since when do we celebrate Valentine’s Day?” Sam’s eyes drop to Dean’s crotch again, a move that doesn’t go unnoticed by his brother.  
  
“You’re right,” Dean says, standing up so fast the chair nearly tips back. “Fuck this.”  
  
Dean goes to Sam, his hands hot on his hips.  
  
“Get up,” Dean says, pulling at Sam so he’s on all fours. He runs both hands up Sam’s back and then down again, circling his waist and then repeating the action.  
  
“Thought it was my ass you wanted?” Sam asks.  
  
“Oh, I do,” Dean replies, giving the side of Sam’s ass a quick smack. “Can you reach the lube?”  
  
Sam stretches over to the bedside table, causing Dean’s hands to fall away. It must spur Dean on to get undressed because when Sam looks back, he’s shoving his jeans and briefs down to his knees.  
  
Turning around on the bed, Sam kneels in front of Dean, putting the lube down next to him. Starting from the bottom, Sam undoes the buttons on Dean’s shirt, leaning in close as he slides it off his shoulders.  
  
Dean leans in too, kissing Sam deeply, then breaking off with smaller softer kisses. He lifts his arms, grabbing the back of his T-shirt and tugging it over his head.  
  
By the time he’s thrown it onto the floor Sam has taken the cap off the lube and is just about to pour it onto his fingers.  
  
“What’re you doing?” Dean asks, enjoying the feel of Sam’s skin as he runs his hands up his arms.  
  
“What’s it look like?” Sam smiles, spreading the lube over his fingers and then taking hold of Dean’s cock.  
  
Dean’s head tips back, exposing more of his beautiful neck. Sam takes the opportunity to lick and kiss up the tendon, while slowly stroking Dean’s cock in his hand.  
  
“Damn it, Sam,” Dean says, husky voiced. Looking back at his brother, Dean brings their mouths together, their tongues meeting this time, and it takes a lot of concentration for Sam to keep jerking him. When Dean kisses, it’s hard to remember anything else.  
  
“M’glad you lost the bet,” Sam says, smiling against Dean’s lips.  
  
“I was tricked,” Dean replies, but there’s no heat in it. In fact, it’s one of the few times when Sam could describe Dean as soft.  
  
Laughing, Sam let’s go of Dean and turns back around, moving a little further up the bed to make room for his brother.  
  
Folding his arms, Sam rests his head on them, sloping his back and keeping his ass up. Dean’s hands feel rough on his skin, but Sam has always liked that.  
  
After stroking Sam’s ass a few times, Dean moves his thumb down to the edge of the plug, adding some pressure.  
  
“Mmm...” Sam swallows, breathing in sharply when Dean does it again.  
  
“Gonna take it out now,” Dean says.  
  
Sam nods, goosebumps breaking out all over his body. He loves this part. Being so exposed, how open it feels afterwards, and the anticipation of what Dean will do once the plug is gone. Sometimes his tongue replaces it, sometimes his fingers, and other times Dean can’t wait and his cock fills Sam back up again.  
  
“So fucking hot, Sam.” Dean eases his fingers around the base of the plug, slowly easing it out. “Good?”  
  
“Yeah,” Sam says, fingers clutching at the bedsheets.  
  
Dean kisses his lower back, the plug coming out smoothly. Sam cries out at the sensation, clenching instinctively at the loss, but then Dean’s fingers are inside him.  
  
Taking his hand off Sam’s thigh, Dean picks up the lube, squeezing some onto Sam’s rim and massaging it in and around. Keeping one foot on the floor, Dean hitches the other leg up so his knee is on the bed. He removes his fingers and strokes his cock a few times before moving the head to Sam’s ass.  
  
“Please, Dean...” Sam pushes back against him, and there’s no mistaking what he wants.  
  
Dean goes agonisingly slow, and by the time his hips are flush against Sam, Sam is swearing into the crook of his arm.  
  
“That’s it,” Dean says, his voice barely more than a whisper. He pulls out a little, thrusting back in but still keeping it slow.  
  
Sam groans, squeezing around Dean’s cock.  
  
“Bossy,” Dean says, running both hands up Sam’s hips and then digging his fingers into the top of his ass.  
  
With a good grip, Dean starts to fuck Sam with more vigour, pulling Sam back onto his cock in time with his hips. He’s not slow or gentle anymore, and judging by the sounds coming from Sam’s mouth he’s not complaining about it.  
  
“Touch yourself, Sam. Wait... let me see you.”  
  
Dean pulls out, his cock twitching against Sam’s thigh. Sam sits up, turning over and then lying down on his back, pulling his knees up. Dean wastes no time getting back inbetween Sam’s legs.  
  
Sam’s head is thrown back, sweat making the skin in his neck glisten, and Dean wants to taste him so bad. But it can wait.  
  
“Dean, fuck me...” Sliding his hand over his chest, Sam finally takes himself in hand, stroking his cock in a tight fist. “Fuck.”  
  
Dean knows the look in his brothers face. He’s close already. Hell, he’s probably been stopping himself from coming all damn day. Dean is more than happy to oblige.  
  
He holds Sam’s legs down, driving back into him at just the right angle that he knows he’s hitting that sweet spot. Sam shudders and bucks, his toes curling up with pleasure.  
  
Dean’s muscles are burning, but he keeps pounding his hips, alternating between watching Sam’s gorgeous cock and the vision that is Sam’s face. In the end, there’s no contest for what gets Dean’s attention.  
  
Sam’s lips are open, bitten and pink. They form a circle every now and again when he blows out a puff air. There’s a blush high on his cheekbones, and his hair is damp where it’s stuck to his forehead. Sam’s eyes though, they’re bright and focused, watching Dean with raw adoration.  
  
“Fuck, I love you, Sammy. Come on, let it go.”  
  
Dean reaches out and touches Sam’s hand, and Sam lets Dean take over. His cock is only barely moving inside him now, but Dean knows just how to finish his brother off.  
  
Sam writhes under Dean, wrapping his legs around his back. He says Dean’s name over and over, before eventually going quiet, his body rigid as his orgasm hits.  
  
Dean watches as Sam comes over his hand, his stomach trembling with each wave of it.  
  
“Ahhh... yes...”   
  
“So good,” Dean says, stroking Sam a few more times before letting him go. “Look at you...”  
  
Sam lies like a masterpiece made into human form, sated and wrecked by Dean’s hands. Dean starts to move his hips faster again, chasing his own orgasm.  
  
Out of the corner of his eye Dean sees Sam put his hand over the plug that had been tossed into the bedding.  
  
“Want you to come inside me, Dean,” Sam says, picking the plug up and running it down between his pecs, lower over his naval, then teasing it against his pubic hair. “And put this back in.”  
  
“Oh, fu...” Dean closes his eyes and his hips slam against Sam’s ass one last time, coming deep inside. “Fuck me.”  
  
“That’s my line,” Sam says, smiling up at Dean.  
  
Dean breathes heavily, steadying himself by putting his hand flat on Sam’s stomach.  
  
“Still going?” Sam asks, digging his heels into Dean’s back.  
  
Dean nods, closing his eyes as his body convulses erratically.  
  
Sam can’t help feeling smug. Winning the bet, great sex, and now seeing Dean like this. It’s been a pretty good day so far.  
  
Exhaling a groan, Dean finally pulls out of Sam and lies down next to him, his head pressed against his bicep.  
  
“You really want that back in?” Dean looks at the plug then at Sam, green eyes glinting.  
  
Sam considers it, but what he’d really like to do now is take a shower, persuade Dean to make dinner, which won’t be difficult, then spend the rest of the night in bed with Dean and a couple of movies.  
  
“Mm, next time. Wanna come for a shower?”  
  
Dean rolls onto his side, leaning on his elbow. He kisses Sam and hums.  
  
“We can still have Valentine’s Day sex tomorrow, right?”  
  
Sam thinks, lifting each eyebrow and scrunching his nose.  
  
“Doesn’t this kinda forfeit that? I mean you lost the bet soooo...”  
  
“I didn’t lose the bet, Sam. I was tricked.”  
  
Sam sits up, scooting off the bed and heading out the door to go shower.  
  
“Sam? Sammy?!”  
  
Sam smiles as Dean continues to call after him. Yeah, definitely a pretty good day.


End file.
